12 Sailing in the Big Island Worth Booking

1.Captain Cook Snorkel On A Power Catamaran With Lunch

★★★★★★★★★★5.0 · 2,232 reviews · 4 hours (approx.) · from $85Our pick

Join Hang Loose Boat Tours for a four-hour catamaran trip from Kona to historic Kealakekua Bay. Captain Aiden, Captain Bryce, Jordan, and the crew guide you to clear water filled with reef fish and coral, with dolphins or winter humpback whales possible along the way. Gear, lunch, drinks, and a boat slide are included.

“Jordan went far beyond in helping my wife and I He is the best Perk and Judy would say he is the best back hand you have”

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2.Deluxe Snorkel & Dolphin Watch Aboard a Luxury Catamaran from Kailua-Kona

★★★★★★★★★★5.0 · 797 reviews · 4 hours 30 minutes (approx.) · from $183

Board Body Glove’s large catamaran from Kailua-Kona for a 4.5-hour outing along the Gold Coast. You’ll get breakfast, lunch, snorkel gear, reef-safe sunscreen, about two hours in the water, and a good chance to spot dolphins or seasonal whales. Captain Erica, Adam, Brianna, and Taylor have all been praised for attentive service, though the Red Hill snorkel site is not Kealakekua Bay.

“There were many snorkeling companies, but I never regret choosing this.The staff were super kind and the breakfast and lunch they provided were so delicious with fresh ingredients. On the way to the snorkeling spot, we could see a group of dolphins. Besides snorkeling, they provided various swimming equipment for children to enjoy. It was a very satisfying experience and I want to do it again!!”

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3.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 722 reviews · 3 hours (approx.) · from $136

Join Sea Paradise at 1:45 pm for a three-hour afternoon sail from Keauhou Bay to Kealakekua Bay. You will receive snorkel gear, flotation aids, reef-safe sunscreen, snacks, and drinks. A crew-led snorkel outing, cultural stories, and possible dolphin sightings round out the trip. Alcohol is available to buy afterward.

“Great snorkel and sail experience! Such a blast and all of the crew was great! I highly recommend this tour.”

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4.Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

★★★★★★★★★★5.0 · 695 reviews · 4 hours (approx.) · from $189

Sail Kona’s coast on Kona Style’s 50-foot catamaran to Kealakekua Bay, where you’ll receive snorkel gear, safety instruction, and about an hour in the marine sanctuary near the Captain Cook Monument. Breakfast, Kona coffee, lunch, drinks, flotation noodles, and Hawaiian history are included. The morning starts at 8:30 a.m. in Kailua-Kona.

“About an hour along the coast to the snorkel site, about an hour snorkeling, and then back (with a few stops along the way). Knowledgable and friendly crew. Stunningly clear and beautiful water. Colorful array of fish and sea life…. Great excursion!”

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5.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 535 reviews · 4 hours 30 minutes (approx.) · from $177

Set out from Keauhou Bay aboard Sea Paradise’s catamaran for a 4.5-hour morning cruise along the Kona coast. You’ll snorkel at Red Hill and Captain Cook Monument in Kealakekua Bay, with gear, reef-safe sunscreen, breakfast, lunch, snacks, and guidance included. Captain T-Roy and crew members such as Beau, Denali, Bailee, and Noe have been praised for their friendly support.

“Amazing grew, fun afternoon. Wish we hadn’t gone a day after a storm - try to go when it’s good visibility, but we still saw nice fish and had fun riding on the boat. Thanks!”

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6.Deluxe Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 472 reviews · 4 hours 30 minutes (approx.) · from $179

Sail from Keauhou Bay aboard Sea Paradise’s catamaran for two snorkel stops near Captain Cook Monument and Red Hill. You get breakfast, lunch, snacks, drinks, gear, reef-safe sunscreen, and fish ID cards. The crew, including captains such as Troy, Mike, and Micah, keeps the outing friendly and safety-focused.

“Excellent crew, great little trip! The ride was amazing, they told us a little backstory about the monument we saw, they were very friendly and approachable. The atmosphere was chill, easygoing, we had enough time to explore the reef, we saw and swum with the dolphins! Definitely worth it!”

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7.Waikoloa Signature Catamaran Sunset Sail

★★★★★★★★★★4.5 · 396 reviews · 1 hour 30 minutes to 2 hours (approx.) · from $159

Sail from Anaehoomalu Bay aboard a 53-foot catamaran for sunset views along the Kohala-Kona coast. The 90-minute cruise includes a premium bar, snacks, shaded seating, restrooms, and live commentary. You board barefoot by tender boat, with room for up to 49 people.

“We had a great cruise. The crew was terrific. We enjoyed the catamaran. The drinks were varied and the dinner was a surprise.”

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8.Afternoon Sail & Snorkel to the Captain Cook Monument

★★★★★★★★★★5.0 · 246 reviews · 3 hours (approx.) · from $136

Set out from Keauhou Bay at 2 p.m. aboard Sea Paradise’s trimaran for a three-hour sail and snorkel at Kealakekua Bay. You’ll receive gear, reef-safe sunscreen, drinks, and snacks, then swim near the Captain Cook Monument in a protected marine sanctuary. The crew offers help for beginners, shares Hawaiian history, and may point out spinner dolphins along the coast.

“The crew staff was amazing! Snorkeling was fun! The staff took the time to explain and of a quick training on snorkeling.”

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9.Kona Signature Catamaran Sunset Sail

★★★★★★★★★★5.0 · 218 reviews · 1 hour 30 minutes (approx.) · from $109

Sail from Honokohau Harbor along the Kona Coast for about 90 minutes aboard a spacious catamaran. Captain Michael and crew members such as Caesar, John, Xander, Nicole, and Kevin have helped create a friendly, relaxed outing. Expect shaded and open seating, a restroom, snacks, drinks, and possible dolphin or whale sightings.

“The boat was awesome. The crew was a lot of fun. The food was really great and the views were unmatched.”

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10.Kona: Captain Cook Reef Catamaran Day Trip with Lunch

★★★★★★★★★★4.8 · 189 reviews · 4 hours - 270 minutes · from $80Best value

Cruise from Honokohau Harbor to Captain Cook Monument with guides such as Bryce, AJ, Aidan, and Kelly. You get snacks, drinks, sandwiches, and fresh fruit, plus snorkeling gear if you choose that option. Expect a lively four-hour ride, local history, reef fish, and possible dolphin or whale sightings.

“The whole team was amazing, we will be back for sure…”

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11.Catamaran Sunset Sail with Cocktails

★★★★★★★★★★4.8 · 68 reviews · 1h 30m · from $159

Sail from Anaehoomalu Bay aboard Hawaii Nautical’s Spirit of Aloha catamaran for a 90-minute sunset cruise. Captain Michael and the local crew serve tropical cocktails, beer, wine, soft drinks, water, and island-style snacks while you watch the Kohala Coast, Mauna Kea, Hualalai, and the Pacific sunset. Boarding involves a short barefoot step through seawater from a tender boat.

“Everything about the sunset sail was awesome. Beautiful sailing and sunset; as well as expert/kind/wonderful captain and crew. I couldn’t have enjoyed it more.”

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12.Waikoloa Catamaran Snorkel & Sail Adventure with Lunch

★★★★★★★★★★4.8 · 39 reviews · 3 hours · from $189

Join Hawaii Nautical’s three-hour Spirit of Aloha catamaran trip from Anaeho‘omalu Bay. Your captain and local crew provide snorkel gear, safety help, lunch, tropical drinks, shaded seating, restrooms, and a freshwater rinse. You will cruise the Kohala Coast, swim over coral reefs, and look for Hawaiian green sea turtles with no prior snorkeling experience needed.

“The captain and crew were fun and informative. They were helpful and put safety of the passengers first while pointing out wonderful sea life including a turtle, octopus, eels, and tropical fish. This was one of the best snorkeling experiences I have ever had! Highly recommend!”

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